Sodium Bicarbonate → 4-Methoxy-2-nitrobenzaldehyde

HRID 1914693

Reaktionsgleichung

Reaktionsgleichung von HRID 1914693
Br[CH:2](Br)[C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[N+:11]([O-:13])=[O:12].C([O-])(O)=[O:16].[Na+]>O>[CH3:10][O:9][C:6]1[CH:7]=[CH:8][C:3]([CH:2]=[O:16])=[C:4]([N+:11]([O-:13])=[O:12])[CH:5]=1

Komponenten

4

Edukt 2

HCID 516892Sodium BicarbonateHCID 35023351-(Dibromomethyl)-4-methoxy-2-nitrobenzene

Produkt 1

HCID 3576914-Methoxy-2-nitrobenzaldehydeAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 1-(dibromomethyl)-4-methoxy-2-nitrobenzene (42 g, 0.23 mol) and NaHCO3 (3 Eq) in water (400 mL) is refluxed for 22 h. The reaction mixture is cooled to room temperature and the product is extracted with EtOAc (2×150 mL). The organic layer is washed with a solution of 1.5N HCl (2×100 mL), water (2×100 mL) and brine then dried over Na2SO4. The solvent is removed under reduced pressure to afford 20 g (85%) of the title compound as a brown solid. 1H NMR (DMSO-d6, 400 MHz) δ 10.03 (s, 1H), 7.93-7.95 (m, 1H), 7.61 (s, 1H), 7.40-7.41 (m, 1H), 3.93 (s, 3H).

Aufarbeitung

  1. temperatureis refluxed for 22 h
  2. extractionthe product is extracted with EtOAc (2×150 mL)
  3. washThe organic layer is washed with a solution of 1.5N HCl (2×100 mL), water (2×100 mL) and brine
  4. dry with materialthen dried over Na2SO4
  5. customThe solvent is removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-810510ceaf56408aadd3a32e6869fdf2
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08614215B2

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